First Time For Everything

My boyfriend and I are very experimental when it comes to finding new positions or sexy role-plays in the bedroom. You could say we have bucket list sex that we constantly add to and check off almost every day! At one point, I really wanted to know what it felt like to take a man from behind the way men have done to me. First, my boyfriend was against it completely. Then, with a little stimulation and a few naughty promises of the future, we tried out strap-on sex for the first time and he loved it! But it was nothing compared to the excitement of taking a big shemale cock for the first time!

First Time Strap-On Sex

Our first time having strap-on sex was so hot! It started with my boyfriend laying back on the bed and stroking his cock to me while I dressed up just the way he liked. I had on a sexy black corset and some nude pantyhose stockings. My high heels with the straps around the ankles drive him absolutely crazy, so of course, I had those on as well. To top off the outfit, I had an 8-inch strap-on cock wrapped around my waist. This strap-on is still my favorite toy because there is another cock on the inside for me to ride while I use the other end on my boyfriend.

Use The Lube

After I was all dressed up, I made my way over to the bed. My boyfriend’s cock was throbbing just from the looks of me. Then, I wrapped my lips around his cock to get him as stiff and hard as he could be. He loves my sloppy sweet blowjobs. This relaxed him from the thought of taking a big strap-on cock in his ass for the first time. I poured some lube from the top of his dick down to the bottom of his balls and rubbed him gently. I worked my way down to his ass and very slowly started to massage the lube around his asshole.

Fucking My Boyfriends Ass

Then, I slid my finger inside of him and started to warm him up for my strap. Like all first times, he was nervous, but he loved how my fingers felt inside of him. Finally, he was ready to take me inside of him for the first time. He turned around, just as I do, and put his ass up for me. I positioned myself and began sliding my cock inside of him. His moans were music to my ears. The power I felt was nothing like the release he felt. Both of us came harder than ever with our first ever strap-on sex!

What’s Next?

As a few weeks went by, more ass play followed our magical night. We wanted to do something special, so we looked into shemale escorts. What is better than a second cock and a second pair of tits in the mix of an exciting bedroom life?

Our Shemale Escort…

Our escort arrived the next night and we invited her in. The three of us sat awkwardly since it was our first time hiring an escort and having sex with a shemale. I was ready to see where the night would take us, so after a few drinks, I took them both by the hand and led them to the bedroom. The thought of her big shemale cock penetrating my boyfriend made my pussy dripping wet.

With a Big Shemale Cock…

My boyfriend and I started to undress in front of her and she slowly started to undo her dress from behind. The three of us stood there staring at the naked and excited bodies in front of us. My boyfriend and I could not keep our eyes off of her big shemale cock standing straight up at attention. She started to stroke it and I walked over to join her. Then as she leaned in for a kiss and our tits began to rub, my boyfriend joined in as well. We all shared deep kisses and it escalated when I began kissing down her stomach to her big shemale cock. I sat there in front of it and began to suck her off while my boyfriend made out with her.

I reached my hand up to pull my boyfriend down alongside me. He is so excited to take her big shemale cock in his ass, but he can’t waste the opportunity to suck one for the first time. He nervously picked up her dick and put it in his mouth. Then, he realized all he had to do was recreate the same things I do to please him. He sucked that big shemale cock until she had to force him to stop. Then he laid on the bed just as he had done for our first strap-on adventure and it was time.

A BIG SHEMALE COCK CUM SHOT

I laid in front of him and spread my legs. His face buried in my pussy as she started to slide her big shemale cock inside of him. She was much bigger than my strap and I know he was hesitant about taking it all the way. The more she pushed, the faster he tongued my clit. After only a few thrusts, I was squirting all over my boyfriend’s face and she was pumping his ass full of cum. My cock crazed boyfriend wasn’t satisfied with only one load. We kept her over or an entire weekend to pump load after load into my boyfriend. He now craves big shemale cock almost daily!

 

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